Chiral Aliphatic Amines Research Articles

A Convenient and Versatile Synthesis of Chiral Aliphatic and Allylic Amines

Preparation of optically pure aliphatic and allylic amines from amino acids is described. Wittig olefination of α-Boc-amino aldehydes affords Boc-protected allylic amines which can be deprotected to the corresponding chiral unsaturated amines. Catalytic reduction of the Wittig product prior to deprotection affords aliphatic amines of high optical purity.

Symmetry rules for chiral aliphatic amines and their salts

1. The sign of the Cotton effect in the circular dichroism (CD) spectra of secondary cyclic amines and the sign of the optical rotatory dispersion (ORD) curve of their salts obey the rule of squares. 2. The sign of the ORD curve of salts of tertiary cyclic amines obeys a sector rule consisting of six sign-determining regions. 3. The sign of the Cotton effect in the CD spectra of tertiary cyclic amines obeys a sector rule consisting of 12 sign-determining regions.